570412-05-4

Basic information

• Product Name: 4-nitrophenyl 2-azido-2-deoxy-β-D-mannopyranoside
• Synonyms: 4-nitrophenyl 2-azido-2-deoxy-β-D-mannopyranoside
• CAS NO: 570412-05-4
• Molecular Weight: 326.266
• Mol File: 570412-05-4.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 4-nitrophenyl 2-azido-2-deoxy-β-D-mannopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: 4-nitrophenyl 2-azido-2-deoxy-β-D-mannopyranoside(570412-05-4)
• EPA Substance Registry System: 4-nitrophenyl 2-azido-2-deoxy-β-D-mannopyranoside(570412-05-4)

Safety Data

• Hazardous Substances Data: 570412-05-4(Hazardous Substances Data)

Upstream product

• 4692-12-0 1,3,4,6-tetra-O-acetyl glucopyranose 
• 87236-45-1 4-nitrophenyl 3,4,6-tri-O-acetyl-β-D-glucopyranoside 
• 53872-80-3 bromure de tri-O-acetyl-3,4,6-α-D-glucopyranosyle 
• 845271-56-9 4-nitrophenyl 3,4,6-tri-O-acetyl-2-O-trifluoromethanesulfonyl-β-D-glucopyranoside 

Downstream Products

• 570412-06-5 4-nitrophenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-mannopyranoside 
• 570412-11-2 4-nitrophenyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-mannopyranoside 
• 50645-66-4 4-nitrophenyl 2-acetamido-2-deoxy-β-D-mannopyranoside 

Relevant articles and documents

A concise synthesis of 4-nitrophenyl 2-azido-2-deoxy- and 2-acetamido-2-deoxy-d-mannopyranosides

4-Nitrophenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α- and β-d-mannopyranosides were prepared from methyl 4,6-O-benzylidene-α-d- glucopyranoside and 1,3,4,6-tetra-O-acetyl-α-d-glucopyranose, respectively. Chemoselective reduction of both azides with hydrogen sulfide readily afforded 4-nitrophenyl 2-acetamido-4,6-di-O-acetyl-2-deoxy-α-d- and -β-d-mannopyranosides in higher yields than reduction with triphenylphosphine or a polymer-supported triarylphosphine. Subsequent de-O-acetylation yielded 4-nitrophenyl 2-acetamido-2-deoxy-α-d- mannopyranoside and 4-nitrophenyl 2-acetamido-2-deoxy-β-d-mannopyranoside in 20% and 44% overall yields, respectively.